Help With a Music Video Script

Hi, I'm in a deadlock right now with a script I'm working on and need all the help I can get.

So, basically I need a way to connect the frames that include the characters (2 main characters) with the frames that include the band. The frames with the characters include their life story, starting from a low point in their life and leading to a good one. The "merge" should happen towards the end of the clip and should last 30 seconds in total (obviously with frames between just with the band or a view).

The locations are not yet set so the answer can be based on whichever location suits your example.

(Ex. One of the characters looks through the window and sees the band playing on a building's rooftop across the street)

Thanks !